3,4,6-tri-O-acetyl-D-glucal

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-D-glucal
• CAS No.: 52485-06-0
• Molecular Formula: C₁₂H₁₆O₇
• Molecular Weight: 272.255
• DSSTox Substance ID: DTXSID501311853
• Nikkaji Number: J558.460D
• Mol file: 52485-06-0.mol

Synonyms:3,4,6-tri-O-acetyl-D-glucal

Chemical Property of 3,4,6-tri-O-acetyl-D-glucal

Chemical Property:

• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 272.08960285
• Heavy Atom Count: 19
• Complexity: 388

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C=CO1)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@H](C=CO1)OC(=O)C)OC(=O)C

Technology Process of 3,4,6-tri-O-acetyl-D-glucal

There total 10 articles about 3,4,6-tri-O-acetyl-D-glucal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

Acetic acid (4R,5S,6S)-2,3,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-4-yl ester → 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-L-arabino-hex-1-enitol (2873-29-2,3685-88-9,4098-06-0,6586-65-8,52485-06-0,86257-90-1,86257-91-2,87335-77-1,87335-78-2,130931-60-1,63640-41-5)

Guidance literature:

Acetic acid (4R,5S,6S)-2,3,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-4-yl ester; With hydrogen bromide; acetic anhydride; acetic acid; at 20 ℃; for 16h;

With copper(II) sulfate; acetic acid; zinc; sodium acetate; In water; at 20 ℃; for 1.5h;

DOI:10.1016/j.tetasy.2006.12.011

Reference yield: 85.0%

acetic anhydride (108-24-7) + (2R,3S)-2-Hydroxymethyl-3,4-dihydro-2H-pyran-3,4-diol → 3,4,6-tri-O-acetyl-D-glucal (2873-29-2,3685-88-9,4098-06-0,6586-65-8,52485-06-0,63640-41-5,86257-90-1,86257-91-2,87335-77-1,87335-78-2,130931-60-1)

Guidance literature:

With 4 A molecular sieve; at 60 ℃; for 20h;

DOI:10.1016/S0040-4039(03)01072-4

Reference yield: 66.0%

2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide (67337-79-5) → 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-L-arabino-hex-1-enitol (2873-29-2,3685-88-9,4098-06-0,6586-65-8,52485-06-0,86257-90-1,86257-91-2,87335-77-1,87335-78-2,130931-60-1,63640-41-5)

Guidance literature:

With 1-methyl-1H-imidazole; zinc; In ethyl acetate; for 30h; Heating;

DOI:10.1021/ja052945s

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-L-glucopyranosyl bromide

peracetyl-L-glucosyl bromide

α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate

acetic anhydride

Downstream raw materials:

(S)-1-(α-furyl)-1,2-ethanediol

(2R,3S,4S)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyran

(2R,3R,6R)-3-(benzyloxy)-2-[(benzyloxy)methyl]-6-phenyldihydro-2H-pyran-4(3H)-one

Refernces

• 1、 -. "Bisindolyl maleimide derivative and preparation method and application thereof". Paragraph 0797. . Retrieved 2017/01/02.
• 2、 Porzelle, Achim,Gordon, Victoria A.,Williams, Craig M.. "Rapid access to in situ generated (R)- and (S)-2-furyloxirane and associated regioselective nucleophilic ring-opening studies". . p. 1619 - 1621. Retrieved 2008/02/05.